


Mister Winger and Miss Edison

by OliviaSprite



Category: Community (TV)
Genre: Brief mention of Jeff and Britta, F/M, Flirting, Friends to Lovers, Happy Ending, I'm new here, Little bit of angst, Oral Sex, Romance, Schoolgirl Kink, Sex, born from the netflix revival of Community, fantasies, season five
Language: English
Status: Completed
Published: 2020-05-22
Updated: 2020-06-29
Packaged: 2021-03-02 22:15:40
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 4
Words: 18,716
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/24314146
Author URL: https://archiveofourown.org/users/OliviaSprite/pseuds/OliviaSprite
Summary: Sure, it was cliche, but a school girl kink was pretty cliche in the first place."What... Annie what are you doing?" Jeff seemed to find his voice, though it was breathier than usual."I came to talk to you about the first paper for intro to law," She smiled sweetly, handing him his papers and fluttering her eyelashes. "Unless you're busy, I can come back later Mr Winger," she added, biting her bottom lip a little.Or, Annie discovers Jeff gets flustered when she calls him Mr Winger and decides to make him squirm. Set just after Season 5 episode two, with mention of season 3, episode 2.
Relationships: Annie Edison/Jeff Winger
Comments: 59
Kudos: 376





	1. Chapter 1

**Author's Note:**

> Hello! This is my first ever fic I'm actually posting. I finally got around to watching Community when they brought it to Netflix, and I binged it all in two weeks and became obsessed with Annie and Jeff. This idea popped into my head during my second binge of the series, apologies if any of the details are wrong, I'm still memorising the ins and outs of the show.  
> Let me know what you think but please be kind, I haven't written fic in a long time. Enjoy!

Annie sighed with annoyance as she looked down at her schedule. She'd joined Jeff's Introduction to Law class to teach him a lesson, but now the other forensics classes on at the same time had filled up. And no matter how big and doe like she made her eyes, the Dean was not letting her overfill a class. As she got deeper into her twenties she noticed her doe eyes worked on less and less people. Though there was one who seemed to still be under their spell.   
Jeff would be so annoyed that she was still in his class. The Dean had promised her that as soon as a spot became available in a different class, he would let her know, but she knew that meant at least another week in Jeff's class. Not that she minded, it wouldn't be hard to do well in Jeff's class, even if he was starting to take it more seriously, but she was worried he might not be as enthused about it.   
Nevertheless, Jeff's class was starting in ten minutes and she had to be there. She needn't have rushed, Jeff was ten minutes late, striding in holding his phone up and texting with one hand and eating an apple with the other. In the right frame of mind, perhaps he could be the image of the stereotypical teacher - but Annie was a bit too fixated on him noticing her, and watching him wrap his lips over the apple - to think about it too much.   
"Okay, so we discussed how to argue in the last lesson, this lesson let's go over Chapter Two in groups," Jeff murmured, not looking up from his phone. Annie hadn't been expecting a huge change in his demeanor, and she didn't want to bother him again, so she kept her mouth shut about doing group work about a chapter reading.   
He still wasn't looking up from his damn phone. Annie didn't want to read too deeply into why she wanted Jeff to acknowledge her so bad - she chalked it up to wanting to do well in the class, it had nothing to do with her attraction to him. That was something she only ever rarely thought about, let alone allowed to consume her thoughts.   
She took a deep breath and stuck her hand in the air. "Mr Winger," She said. She watched as Jeff slowly looked up, confusion clear in the way his eyebrows knitted together. "Since I missed the end of the last class, are there any notes I can look over?" She asked. The whole class was looking between the two, remembering their argument only a few days before. It was like they were waiting for a pipe to burst, or mainly just for Annie to storm off again.   
Jeff seemed to collect himself. "Annie you can uh..." he trailed off, obviously still a little confused. Annoyed? Oh God was he annoyed? He flicked his eyes around the room, seeing how everyone else had already partnered up to read over the chapter. "Come here," he sighed.   
Annie quickly stood from her desk, walking over briskly and shooting a look at Garrett so he'd stop staring at them, obviously trying to eavesdrop. She stood next to Jeff, biting her bottom lip.   
"Okay so there's no other empty forensics classes during this time slot, so the Dean said I have to stay in here until one opens up," Annie explained before Jeff could say anything. "I promise I'll try and lay low Mr Winger," she added. She noted how Jeff tensed, his eyes flicking up away from her face and his fingers tightening ever so slightly around his phone.   
"Why are you calling me that?" He asked. Annie raised an eyebrow.   
"You're my teacher, in class time I'll respect that," She chuckled. Even if she didn't think Jeff was the best teacher, and he was her friend and...whatever else, before he was her teacher, she didn't want to disrespect his position, she always had that respect for teachers. She didn't particularly like it either, thinking it made her sound younger again. The last thing she needed was reminding Jeff of her age, but she couldn't bring herself to refer to him by first name in class. What if the other students thought she'd get a better grade because of their friendship?   
"Does it bother you?" She asked.   
"No," he answered quickly, not meeting her eyes.   
"Mr Winger I promise I'll-" She was cut off by Jeff standing up and walking towards Garrett and his partner.   
"Garrett, Miss Edison is going to join you," he said firmly. Annie began to walk over, grabbing a seat to pull up next to Garrett.   
"My last name is-" Garrett began.   
"Don't care," Jeff said firmly, eyes flicking to Annie with a strange look before briskly walking back to his desk. 

Annie tried to talk to Jeff after class but he left before she'd even risen from her desk. She was perplexed. Was her being in his class that bad? That couldn't be it, he'd tell her that at least. Jeff wasn't one to shy from the truth, even if it was hurtful. She thought about how tense he'd been, and confused, when she called him Mr Winger.   
A memory rushed to her mind of the two of them working on beating Annie Kim for the Model U.N. competition. She often thought about that day, how comforting Jeff had been, how supportive. How he'd somewhat confessed his feelings for her in the study room and cupped her chin affectionately. It was a bitter sweet memory for Annie. She'd been embarrassed by her behaviour, but had enjoyed the moment she'd shared with Jeff.   
"You're acting like a little school girl, and not in a hot way," he'd shouted.   
She'd thought about it before. School girl kinks were pretty well known, and she'd seen her fair share of school girl costumes and props when she'd lived above Dildopolis.   
She thought about how tense Jeff had been when she'd called him Mr Winger, and how he'd referred to the little school girl thing as a turn on - well, would have been if Annie hadn't had a rather unattractive tantrum instead in front of the school.   
There were few people she could talk to about her feelings for Jeff. She could go to Abed of all people when Jeff's behaviour confused her, he seemed to understand it better than most. She could talk to Troy about general 'boy trouble', though a lot of his advice wasn't what she'd associate with Jeff.   
She knew there was one person she could talk to when it came to Jeff Winger and sexual fantasies. And she didn't particularly want to, but she had to know. 

"Hey Britta, how are you?" Annie managed to find Britta in the study room - alone, thank God. Britta looked up from her psychology text book she was reading. Annie tried not to be jealous of Britta, but it was hard. She was gorgeous, and in the stereotypical way too. Blonde, blue eyed, mature but an airhead in the kind of hot way guys liked. She had been Jeff's perfect type once upon a time - maybe she still was, Annie tried not to listen to Jeff's stories about what - or who - he did on the weekend.   
"Hey Annie, what's up?" Britta asked.   
Annie took a deep breath. Would Britta want to talk about this? Would it be weird? Would she tell Jeff? She sat down across from Britta.   
"So... remember how you slept with Jeff?" she started, cringing at how it had tumbled out with a slight bitterness in her tone.  
"Somewhat begrudgingly yes, I remember," Britta replied, her left eyebrow cocked and confusion clear in her voice.   
"Did he ever have any..." Annie trailed off, trying to think of the best way to phrase it. She fiddled with the strap of her bag. "Fantasies?" She finished.   
Britta laughed. Laughed! Annie would be offended at Britta laughing at her struggle if she wasn't aware that Britta didn't know she was struggling in the first place.   
"A few, I guess," Britta chuckled when she replied. "Since when do you want to know about my sex life with Jeff? It's rather unspectacular, he avoids all eye contact and won't let you wear any of his clothes after," she rolled her eyes. Annie somehow wasn't disheartened by that information. Somehow she couldn't shake the idea of sex with Jeff being rather spectacular, even without eye contact or stealing his clothes.   
"Well... okay so today in class, I called him Mr Winger, because he's my teacher and he kind of... tensed, I don't know," Annie tried to explain. "So I was wondering if he was into the whole," she paused, shutting her eyes for the next part, "schoolgirl thing?"   
There was silence. Annie opened her eyes again and saw Britta looking at her in disbelief.   
"You wanting to participate in a fantasy about being a schoolgirl for Jeff does not make me feel less grossed out by whatever is going on with you two," Britta grimaced.   
"Is he into it or not?" Annie asked, impatient. She was sick of people being grossed out by herself and Jeff. God, she wasn't eighteen anymore, she was a young adult who was perfectly capable of making her own decisions. "I'm not trying to participate in anything," she lied, "I just want to see him squirm a bit," She added, which was the truth. If Annie could make Jeff Winger feel the least bit flustered, she'd take that as a win whether anything came of it or not.   
Britta stared at Annie for a moment more, before sighing. "I don't know for sure, but with you, yes, he's probably into it," Britta replied. "If you want to make him squirm you should dress the part," she added, seemingly coming round to the idea if it meant messing with Jeff. She grabbed her phone and looked up a picture of a naughty school girl outfit, showing it to Annie.   
"Britta! I can't wear that to school! It's too obvious, and the Dean will probably send me home," She protested.   
"He'd probably make you give the costume to him first," Britta chortled. Annie stood up with a huff. She hadn't even really gotten a real answer, and now Britta knew Annie's plan.   
"Don't tell Jeff about this okay?" Annie requested as she began to leave the room.   
"Knock him dead!" Britta called with a laugh, going back to her book.   
Annie rolled her eyes, and then rolled them a second time when Britta texted her the picture of the costume. No way. It would be so obvious what she was trying to do. She looked the costume over one more time. There was no reason she couldn't use elements of it though. 

Annie tried to look more confident than she felt. She knew she looked hot. She wasn't so naive to think that this outfit wasn't doing wonders for her. But she'd never dressed like this before, let alone walked through school in it, in the hopes of flustering her friend, her crush, her bloody teacher!   
She'd gone with a short black tennis skirt that just hit her mid-thigh, black knee high socks gathering up over her knee. She'd put on her usual flats, knowing that keeping their height difference would work in her favour. She'd tucked a white button up shirt into the skirt, but unbuttoned quite a few. As it was, the shirt was a little old and therefore slightly see-through, showing hints of the white lace bra she was wearing underneath. It was more subtle than the tartan-booty-skirt-and-white-tied-up-top-with-no-bra combo that Britta had sent her, but she still felt like it would do the trick. If the gazes following her down the hall were anything to go by, she was right.   
She didn't have a class with Jeff today, but she wanted a bit of privacy for this outfit reveal anyway. She peered her head around the corner, smiling when she saw Hickey leaving the office he shared with Jeff. Despite his crass nature, Hickey seemed to stick to his schedule for his classes. Not for the first time, she was thankful she'd noted down his class schedule when Jeff had brought him into the study group. Sure, then it had been to help organise social arrangements, but now it was for getting-Jeff-alone-arrangements.   
Annie swallowed thickly once she reached the door of Jeff's office. She rapped a tune with her knock.   
"Come in?" Jeff called, obviously surprised because Greendale students didn't usually knock.   
Annie swung the door open slowly, biting back her smug smile when she saw Jeff's eyes widen, very obviously looking her up and down from where he was standing next to his desk.   
"Can I talk to you for a second Mr Winger?" Annie asked, her voice taking on a slightly higher pitch that she'd used on Jeff before.  
Jeff lost his grip on the papers he'd been about to pick up, the stack fluttering to the ground, but Jeff didn't take his eyes off Annie.   
"Oopsies," she giggled, rushing forward and bending down with her ass remaining in the air to scoop up the papers. Sure, it was cliche, but a school girl kink was pretty cliche in the first place.   
"What... Annie what are you doing?" Jeff seemed to find his voice, though it was breathier than usual.   
"I came to talk to you about the first paper for intro to law," She smiled sweetly, handing him his papers and fluttering her eyelashes. "Unless you're busy, I can come back later Mr Winger," she added, biting her bottom lip a little.   
"Annie, Christ," Jeff breathed, shamelessly looking her up and down again. He quickly moved behind his desk, seeming to think a bit of space between them would help his cause. It didn't, Annie perched herself on the edge of his desk, her skirt riding up a little higher and fanning onto the wood.   
"I just wanted to make sure it's okay that I'm in your class now," Annie continued on, fiddling with a pencil on his desk, stroking over it with slight insinuation. Okay so she'd watched a few schoolgirl porno's when she got home. Whatever, it was research. "I'd hate to be a bother for you," she smiled, flicking her eyes up to meet his.   
Jeff still seemed a little stunned. Then, he seemed determined.   
"It's not a bother, Miss Edison," he finally spoke, his voice taking on a slightly deeper drawl as his hands slid into his pockets. "I only hope you'll be able to keep up with the work," he said, eyebrows raising almost in challenge. Annie steeled her gaze, then let out another girly giggle.   
"Well you could always be my private tutor if I get lost can't you?" She asked, cocking her head to the side. Jeff pursed his lips, slowly stepping back around his desk to stand in front of Annie. Annie turned her body so she was sitting completely on the desk, legs only slightly open in invitation.   
"This is a dangerous game you're playing Annie," Jeff said under his breath. It was a warning, Annie heard it as one. He was losing his resolve, he was letting her know he wouldn't be able to hold back much longer.   
Annie wasn't nervous, she wanted this. Despite being dressed as a schoolgirl, she'd never felt more mature in her life. She'd gone after what she wanted, and she wanted Jeff.   
The fact that he seemed to finally be understanding that, made her feel even hotter.   
"I understand, sir," she smirked. The sir seemed to have been the final straw. Jeff walked forward, hands finding Annie's knees. Annie automatically parted them more, using the heels of her feet to pull him between them. Jeff's hands slid up her thighs, finding purchase on her hips.   
"You look..." he struggled to find the words, "indescribable," he breathed with a small chuckle.   
"You like it?" Annie hummed, daring to lean forward a little and press small, soft kisses to the curve of Jeff's neck. Small steps, she'd learned. A full on mouth kiss might scare him off, the idea was to get him to initiate it.   
"I both like it and hate that other people saw you in it," He confessed, squeezing her hips. Possessive. Well that wasn't new, Jeff was always protective of her, it was only natural for possession to blur into that as well. It made Annie's cheeks heat up, the pink spreading down her neck to her breasts that were nearly spilling out of her shirt. The push up bra had been a good choice.   
"Don't worry, I'll only wear it for you from now on Mr Winger," She reassured, her hands sliding up his toned stomach and resting on his chest. He was so strong, so firm against her hands. So much taller, bigger than her. It was so attractive. She pulled her lips back from his skin, meeting his eyes briefly before he connected their mouths urgently. She moaned into the kiss, sliding her hands up over his shoulders to tangle in the ends of his hair. Her heart was beating like a drum in her chest and she wondered if Jeff could hear it, feel it. Every touch of his hands felt like electricity, tracing her skin through her clothes. His hands moved from her hips to slide down onto the desk, caging her in and gently pushing her onto her back so she was lying flat on the desk. Annie instinctively wrapped her legs around his waist, her mind racing with 'yes, yes, finally, yes.'   
And then it was gone.   
Annie's eyes flew open as Jeff pulled back from her, taking a few steps back from the desk, his hands rubbing over his face. Annie sat up, her eyebrows pulled down in a deep frown. She knew that look, she knew what was coming.   
Suddenly she felt so stupid. Of course a schoolgirl costume wouldn't work. It only reminded her of their age gap. That stupid age gap everyone loved to remind her of.   
"Annie-" Jeff started.   
"Yeah I know what comes next, save it," Annie sighed, getting off the desk and smoothing her skirt down. Tears pricked her eyes but she held them back. No more crying because of Jeff fucking Winger. At least not in front of him.   
"Annie, I'm trying to be the good guy here," Jeff groaned, hands dropping from his face and crossing in front of his chest instead. Something inside Annie snapped.   
"Oh you know what Jeff, a good guy would let me make my own decisions!" She hissed. "A good guy would understand that yes, I'm young, but I'm old enough to know what I want. I'm so sick of this age gap excuse, it didn't matter for Britta and Troy, and their age gap is only slightly less than ours!" She pointed out, picking up her bag. "So what reason is left Jeff? If you don't want me I'd rather you just said it."   
"You're technically my student, I could be fired," Jeff protested weakly. Annie rolled her eyes in utter disbelief.   
"God, you know what, Britta said sex with you was pretty unspectacular, maybe I shouldn't even be bothering," she muttered. It was a snide remark, but Annie was finished with this. She couldn't feel like the desperate girl with a crush anymore. She wanted to feel wanted too.   
"What, Britta said that!?" Jeff cried. "Why were you talking to Britta about our sex life?" he asked after a moment, moving to block the doorway so Annie couldn't leave.   
"Because, I wanted to know if this was a fantasy of yours," Annie rolled her eyes, crossing her arms. "Whatever, mission accomplished, this fantasy would probably work if it was Britta, God knows she's good enough to sleep with," she mumbled. Jeff's face fell.   
"Annie this was never a question of whether or not you were good enough," He said earnestly, reaching forward and holding her elbows. "In fact, it's the opposite, you mean more to me than Britta, you're not... I could never just sleep with you and have it not mean anything," he confessed, looking into her eyes.   
Annie could feel herself melting. She didn't want to give in, but Jeff always had a way with words. He had his famed Winger speeches after all.   
"Then what's in the way?" She breathed, trying to remain quiet, scared any loud noise could break them apart.   
And it did.   
"Dean dong!" Dean Pelton's voice cut through their reverie, making Jeff jump almost a mile back from Annie. "Miss Edison, changing your look I see, where did you get that skirt from?" the Dean asked.   
"You can have it, I don't need it anymore," Annie mumbled, pushing past the two without looking back. 

It was times like this Annie wished she was still talking to her mom. Abed and Troy were leaving her alone, and she understood why after she'd charged into the apartment, slamming the door to her bedroom behind her. They knew if she wanted comfort, she'd keep the door open a crack, it was their unspoken rule. There was no way she could talk to Britta about today, she couldn't admit that she'd failed to the girl who had gotten Jeff without any effort at all. And she knew Shirley wasn't an option - she'd probably be praying for her already if she saw her in that costume today. Her mom wouldn't even be particularly helpful, but she'd listen, and she'd tell Annie that it was going to be okay. Annie rolled over in her bed, staring up at the ceiling. She then looked down a the pink, fluffy sheets on her bed, and the stuffed toys that surrounded her. Would getting rid of these things make Jeff want her more? Maybe if she had a more sophisticated bedroom, he'd be interested. She'd seen Jeff's apartment - it looked like something straight out of a catalogue, chic and very...adult.   
Annie sat up with a groan. No, she didn't want to change who she was for the interest of a guy. Annie knew she was an adult, in some ways, more adult than Jeff. She didn't need to change a thing.   
"Annie," Abed spoke up from outside her room. In hindsight, she wished she'd just answered from behind the door, but instead she got up and pulled it open.   
To see Jeff and Abed standing on the other side.   
Gone was her sexy, schoolgirl costume from today, instead replaced with her green matching pyjama set with frogs printed on them. She was embarrassed for a moment but then remembered her revelation from only minutes before. She loved her frog pyjamas, and just because she was wearing them didn't make her any less of an adult. She crossed her arms, staring Jeff right in the eyes to exude the same confidence she'd had in her outfit earlier.   
"Can I talk to you?" Jeff asked. Annie pursed her lips then nodded. She stepped back to allow him to come into her room, rolling her eyes at how his gaze lingered on her stuffed animals. She shut the door behind her, hissing to Abed and Troy not to listen.   
She turned to look at him, noting he was dressed rather nice. He was in a fitted navy button up, and black trousers.   
"Got a hot date?" Annie muttered, not bothering to hide her annoyance.   
"Possibly," Jeff replied, looking down at her. Annie forced a tight smile.   
"Lucky her," she sighed.   
"More like lucky me," Jeff's gaze was unwavering upon her. Annie was over this, why had Jeff come all the way here to tell her about his date after what had happened today?   
"What do you want Jeff?" Annie asked.   
"We've established that, a hot date. I came to ask you to dinner," Jeff said it rather quickly, a trace of nervousness in his tone. Annie's breath hitched and her eyes widened. Her heart couldn't help but soar, the idea of going on a date with Jeff Winger was everything she'd wanted for so long. And yet, she couldn't shake her annoyance with him.   
"Not if I have to change who I am Jeff," She replied after a moment's pause. Jeff's face flickered from disappointment to confusion.   
"What do you mean?" He asked.   
"I mean all this," Annie said, gesturing to herself and her room. Admittedly, Jeff stuck out like a sore thumb, all older man and monochrome in a bedroom straight from a Disney film. "I like how young at heart I am, I love this stuff, I love pink, and cartoon frogs, and stuffed animals. And none of that takes away from how smart, mature and... adult, I am," She said firmly, keeping her eyes focused on his. This was her time to be confident, she couldn't look away and let him think she wasn't serious. "And none of that stuff is going anywhere, so if that freaks you out, if you can't handle-"   
She was cut off when he leaned down and kissed her.   
It was a sweeter kiss than before in his classroom. It wasn't dirty, or lust filled. It was tender, and sweet, and he held her face like it was made of glass.   
Annie's eyes fluttered back open when he pulled back to look at her, his hands still cupped on her cheeks, his right thumb stroking circles.   
"I don't want you to change a thing," he breathed. "I don't want you to change who you are for anyone, I don't want you to try and be like Britta, or Slater, or anyone other than you. You're... amazing the way you are," he promised.   
"Jeff," Annie breathed, biting down on her bottom lip.   
"Let me take you to dinner, I'm done pretending I'm the adult out of the two of us, and I'm sorry for thinking otherwise for so long," he chuckled softly. Annie smiled, she'd had a similar thought before, and it reminded her of what a great team they were.   
"Okay," she whispered, nodding slowly. Jeff smiled wide, connecting their lips together once more. She pulled back. "As much as I was just going on about how I love my cartoon frogs, I doubt wherever you're taking me will allow this kind of attire," she chuckled.   
"While they are adorable, yeah you'll probably have to change," he smiled, taking her hand and squeezing it. Annie nodded, looking up at him, still in disbelief that today had lead to this. She'd thought she was going to end up sleeping with Jeff, and instead she'd ended up with a date.   
"I'll meet you down at my car Miss Edison," he whispered, leaning their foreheads together.   
"Be down in a moment Mr Winger," She purred back cheekily and he let out a breath.   
"You're going to be the death of me," he groaned, pulling away from her and walking to the door of her room. He turned back to look at her once, before leaving the room and heading to his car. She giggled to herself and began to get ready, sending off an email in reply to the Dean before she did so:   
'Sorry Dean, I've decided to keep the skirt. Annie.'


	2. Chapter 2

**Notes for the Chapter:**

> It's here! Thank you for your patience. This chapter covers their first date, and is told from Jeff's perspective. Hope you like it and thank you so so much for the support on the first chapter - I really didn't know what the response was going to be like on my first ever fic, and it was all so lovely and positive, it made my day every day I got a comment or kudos.

Jeff took a deep breath once he reached his car parked at the bottom of Annie, Abed and Troy's apartment building. Just moments ago he'd been down here pacing, trying to find the guts to go up there and tell Annie how he felt about her. To officially ask her on a date.   
He hadn't thought today would end like this. Sure, yesterday when Annie had called him 'Mr Winger', he knew he'd been less than subtle with how it had affected him. He hadn't even realised how much it affected him until he heard it coming from Annie's mouth. He hadn't expected Annie to show up to his office today, dressed so un-like herself that if he hadn't have been turned on, he might have sat her down to ask her if she was feeling okay. Jeff had meant what he'd said upstairs. He liked the clothes Annie usually wore, he liked her young-at-heart nature and somewhat innocent personality - he'd just realised now that he wasn't a monster for liking those things.   
Annie had been right. Just because she was like a Disney character personified didn't mean she wasn't an adult. Jeff had seen Annie conquer with her intelligence, her curiosity and her resourcefulness. In many ways, she was more mature than him, and she made him a better man.   
Sure, the school girl costume was a nice touch, but she never had to know he'd never really found that sort of thing hot until he saw it on her. Or maybe he would tell her if it helped her feel more confident - and if it meant she'd wear it again.   
Jeff was leaning against his car when Annie came out of the building. Jeff's heart lurched and his lips parted a little when he saw her.   
Annie was beaming at him in a strapless dress that was tight around her body to just above her waist, before it hung loose and fell to just above her knee. It was a forest green with small delicate flowers embroidered around the hem, and she matched it with heels that only made her slightly taller. Jeff would never admit to loving how much smaller she was in height, but he had a feeling she already knew. Maybe she would be able to explain to him why he loved it sometime.   
The outfit was so wonderfully Annie with a touch of sexy first date thrown in there, Jeff was seconds off getting on his knees and professing his love for her.   
God, let's start with, "Milady," he smiled.   
She was already smiling at him, and when she fluttered her eyelashes at him Jeff knew he was a goner. "Milord," She hummed back, walking towards him.   
Jeff gave himself permission to look her up and down again as she came closer. He was allowed to do that now.   
"You look beautiful," He cleared his throat. Annie smiled and looked down at herself for a moment before flicking her eyes back up to Jeff's.   
"Your reaction gave that away," She teased. Jeff chuckled.   
"One little kiss in her frog pyjamas and Annie Edison has all the confidence and wit in the world," Jeff teased back, opening the car door for her. He loved seeing her so confident, not comparing herself to Britta or Slater anymore. Jeff didn't want them, he wanted Annie, and he'd spend all night continuing to prove that to her if it kept her feeling this good about herself.   
Annie slid into the car and Jeff closed the door behind her. He took another deep breath as he walked around to the driver's side. Here we go, he thought. 

They drove in relative silence. Every now and then, Jeff caught Annie looking at him out of the corner of his eye, and he was sure she was catching him doing the same to her. Jeff felt like he was a seventeen year old boy again going on his first real date. But he knew this wouldn't be just any other date. This was a date with Annie Edison, one of his best friends. This date mattered possibly more than any other.   
When they arrived at the restaurant, Jeff jumped out first and half jogged over to Annie's side to get the door for her.   
"Such a gentleman," She hummed as she got out, giving him a smile.   
"I know, look what you do to me, I'll be reciting sonnets about your eyes soon," He joked with a chuckle, placing his hand on her lower back to lead her into the restaurant. Annie's cheeks turned a deep shade of pink at his joke, and if they weren't at the door of a pretty fancy place he might have pressed her against his car and smothered those pink cheeks with kisses.   
He needed to get a hold of himself.   
"This place is fancy," Annie voiced his thoughts aloud as they began to walk up the steps towards the front door. "This impress a lot of your dates?" She asked.   
"It doesn't impress you?" He asked back, somewhat nervously. Annie rolled her eyes with a chuckle.   
"Jeff you could take me for burgers in a back alley and I'd still enjoy it, I enjoy spending time with you, doesn't matter where," She insisted. Jeff wondered when their roles had switched and he had become the insecure, worried person in their pairing. He wondered if it'd always been that way and he'd been too arrogant to notice.   
They were guided to a seat inside the restaurant. Jeff could tell Annie had never been anywhere like this before as he watched her glance over the velvet red curtains, dimly lit booths and fancy cutlery. They took a seat in one of the dimly lit booths, Jeff letting Annie slide in first before he scooted in beside her.   
"Shall I start you off with some wine?" The waiter asked, his eyes lingering on Annie in a way Jeff didn't like.   
"I don't know how to pronounce any of the wines on this list," Annie chuckled as she looked at the drinks menu in front of them. Jeff quickly glanced at the wine list over Annie's shoulder, then ordered one of the simpler ones - a little cheaper on his wallet but also not too strong for what he assumed Annie would enjoy.   
"Great choice sir, same for your daughter?" The waiter asked, his question bringing a pang low in Jeff's stomach that simultaneously made him want to throw the drinks menu at the waiter's face and curl up in a ball and cry.   
"I trust that my date can pick out a good wine, so yes, two glasses please," Annie corrected firmly, handing the drinks menu to the waiter with a steely force in her eyes that Jeff had learned long ago meant Annie was pissed at you. He tried not to be at the receiving end of that look too much, but he also knew how to get himself out of it a lot of the time.   
The waiter walked off with a disappointed look on his face. "Jeff don't worry about it," Annie said softly, resting her hand on his knee.   
"Don't worry about you getting called my daughter when we go on dates?" Jeff huffed wryly.   
"Oh I don't know, being called daddy is a turn on these days isn't it?" Annie smirked, squeezing Jeff's knee. Jeff's brain fizzled for a moment and he felt his mouth drop open slightly, just as the waiter returned with their bottle of wine, and glasses. Jeff let Annie do the thanking as their glasses were poured, and when the waiter left she took a sip of wine and flitted her eyes back to Jeff.   
"This wine is lovely," She hummed. She let out a small giggle, "What?"   
"Sorry, it's taking my brain a while to register Annie Edison being so...dirty," He chuckled. "I've been overloaded with it in the past 24 hours," he pointed out.   
"Oh please, Jeff, I once made out with you so you would drop a paraplegic and we would win a Community College debate," She laughed as she sipped her wine again. "I'm not as pure as you think I am," she hummed.   
Jeff thought back to that day, their first kiss, the first moment Annie had burrowed her way into his heart. How did he not realise back then how darkly manipulative Annie could be to get where she wanted to go? How did he not realise that after all the times she'd fluttered her big blue eyes at him and he'd done her bidding?   
"I'm slowly learning that," Jeff murmured, picking up his wine and taking a sip himself. He congratulated himself on a good choice, it was enough to take the edge off but not enough to overpower them both. He wanted to remember tonight.  
The conversation flowed easily after that. Jeff asked Annie about her criminology classes, Annie laughed as Jeff told her about Hickey's cartoon drawings he'd found on his desk, they drank their wine and both ordered a salad before Annie convinced Jeff to share a dessert with her. Damn those big blue eyes and fluttery eyelashes.   
Her hand had barely left his knee, and Jeff's arm had somehow made its way to rest on the seat behind her. And the world didn't explode, no one glared at Jeff or called him a monster, even the waiter seemed disinterested by the time he bought them the cheque.   
Jeff had never had a date feel so perfect. He hadn't thought once about taking her home - well that was a lie, he'd thought about it every time her hand inched a little higher up his leg, but he also didn't care if nothing happened. Tonight had been perfect.   
They'd talked about their friends, Shirley's situation with Andre; Troy and Abed's latest antics; but they seemed to both stay away from discussing Britta.   
Jeff would be lying if he said he wasn't mad Britta had told Annie that sex with him wasn't spectacular. It wounded his ego, but he also knew that while he had cared about Britta's enjoyment, Annie's enjoyment would probably be more important to him than his own, which hadn't been the case with Britta. She was fun but Annie was everything, and he didn't want her to think he wouldn't give her everything in that department.   
"It's a nice night, want to walk through the park before we leave?" Annie asked when they stepped out of the restaurant. Jeff nodded and smiled when their hands tangled together automatically, like they'd been doing this forever.   
There was something about late night walks, they brought out the emotional in a lot of people. Jeff tried to be the exception to the rule, but Annie seemed to bring everything out in him - emotion and turmoil included.   
"So uh, I know Britta left a pretty bad review about my sexual skills-" He began.   
"Don't worry about it, I'd rather we didn't talk about her," Annie quickly interrupted. Jeff frowned and squeezed her hand.   
"Annie, that 'her' is our friend, and we'll have to see her in a couple of days-"   
"I know, just not tonight, tonight has been-"   
"Perfect, yeah?" Jeff interrupted her, stopping to face her, smiling down at her. She smiled up at him too, nodding slowly. "Annie I don't want you to compare yourself to Britta," Jeff said, moving to hold her shoulders and bring her closer. Annie licked her lips and leaned into his touch.   
"You would have slept with her if she'd come to your office wearing that outfit today," She whispered.   
"Yes, probably," Jeff admitted. "But only because it would be fun," He added. Annie frowned at him, moving out of his hands. "No, no, wait, not that it wouldn't be fun with you, God Annie do you know how much willpower I needed to not have you right there on my desk?" Jeff quickly tacked on, realising he'd messed up. He pulled Annie back towards him, resting his hands on her sides. "What I meant was, Britta is...was just fun, I didn't care about her the way I care about you. I didn't take her on a date, I never tried to romance her, I certainly never got jealous if young, hot waiters tried to hit on her," he chuckled at the end. Annie's eyes widened a little.   
"You were jealous of the waiter? That's so-"   
"Do not say cute," Jeff interrupted. Annie bit her lip and poorly held in a giggle. Jeff smiled down at her and gently reached up and pulled back her hair behind her ear, leaving his hands on her cheeks. "It's probably going to take me a while to be good at this stuff, but that's the difference between you and Britta, I'm willing to try for you, more than willing, I want to do everything I can to do this right for you," He breathed. Annie looked up at him like he was handing her the world, and he kind of was.   
"I'm patient," She whispered. "And I'm happy to help you be good at this," she added with a light giggle. Jeff was a sucker for Annie's giggle, so he leaned in and kissed her. Annie responded, sliding her hands up to hold his biceps. He stroked his thumbs over her cheeks, and his stomach swooped when she hummed into his mouth.   
"Jeff," She whispered when he pulled back.   
"Yeah?" He breathed.   
"Take me home." 

The door to Jeff's apartment slammed against the wall when he and Annie burst through it. Jeff broke their lips apart for a moment to close the door, before pushing her against it and kissing her deeply again, their tongues sliding together.   
Annie's moans made his knees weak everytime she let one out. Her hands had slid up to tangle in his hair, his scalp prickling from every tug. She hitched one leg up around his waist and Jeff took the hint and picked her up, holding her under her thighs, still pressed against the door. This was why he loved how small she was in comparison to him.   
"I love how easily you can man handle me," she giggled against his mouth, as if reading his mind. She resumed their kissing and bit down on his bottom lip and Jeff's knees actually did wobble a bit. He held her firmly against him and began to carry her over to his bedroom. He tripped on a sock in his doorway and toppled them both onto the bed. It must have looked intentional because Annie moaned even louder and began sucking at the base of his neck, tightening her legs around his waist. Her dress had hiked up and he could feel her wetness against his stomach where his shirt had ridden up. His dick was becoming painfully hard in his jeans, and he just wanted her naked now and he wanted to touch her and kiss her and he wanted-   
"Annie," Jeff breathed, pulling back a little.   
"Jeff Winger don't you fucking dare-" Annie practically growled out.   
"No, no, Annie, I'm not about to stop this," He assured her, squeezing her hip. He quickly got over the shock of hearing Annie swear like that, and the realisation of how hot it was when she swore. He was quickly realising everything with Annie was either cute or hot or both.   
"What's wrong?" Annie asked, sliding her hands up his biceps and resting one on his shoulder and one on his cheek. He turned his head and kissed the inside of her wrist.   
"We should slow down a little," He breathed.   
"What? Why? That was hot," Annie asked, her eyebrows knitting together.   
"Yeah it was but... I don't want you to think I'm just trying to get in your pants, we can take this slow or I can light candles and make it sweet if that's what you want-" He was interrupted by Annie leaning up and kissing him quiet.   
"Jeff Winger," She whispered against his lips, connecting their eyes. "I'm not eighteen, I've had sex more than once, I've done sweet, I've done fast, I've done things in between," She was assuring him now, so quickly the tables had turned. "I haven't done you," She giggled a little and Jeff couldn't help but laugh softly too. "I don't need candles, I don't need grand declarations, I need..." she trailed off then smirked, a glint in her eye making Jeff's heart skip a beat. "Jeff I need you to give me the most spectacular sex you possibly can."   
God Annie knew exactly what she was doing. A manipulative little doe-eyed Disney princess as always, who had Jeff wrapped around her finger, and he didn't even care that he was totally going to give into her challenge.   
He leaned in and kissed her, pressing her back down onto the mattress and using his grip on her hip to slide them both further up the bed. She tangled her hands in his hair again and Jeff gasped whenever she gave a slight tug. His hand trailed up her back and then he worked the zip of her dress back down. Annie helped him by pushing the dress down her body, wiggling it down and off her legs along with her shoes. Jeff steeled himself. He was about to see Annie Edison naked. And he was going to be allowed to touch her.   
His eyes flicked down to her chest, and he wasted no time in attaching his lips to her nipple, reveling in her moans as he sucked. He used his free hand to tug at the other one.   
"Fuck, Jeff," Annie whined, and it was even hotter hearing Annie swear when he knew he'd been the one to do it. He moved his mouth to the other nipple and grabbed a handful of her breast he'd just finished with. Annie's back was arched, as if she was trying to push her breasts more into his mouth and hands. He wondered if he could make her finish just from nipple play. Before he could ponder that idea further, Annie pushed him back and tugged at his shirt. He straightened up and whipped it over his head, and he couldn't help but smirk at Annie ogling him. She reached up and ran her hands down his chest and abs, fingers tracing over his V-line and stopping at the waistline of his jeans. She suddenly looked a little nervous.   
"You okay?" He asked softly. She nodded.   
"Yeah just... you're a lot more...man, than I'm used to," She confessed with a small chuckle. Jeff felt himself blush. Fucking blush.   
He took her hands gently and guided her to unzip his jeans. Her hands slid down of her own accord and cupped him, her thumb stroking over his bulge slowly. He gasped and rocked into her hand a little. Then he remembered her challenge.   
He climbed off the bed and pulled the rest of his jeans down, leaving them in a pile with Annie's dress. He gently leaned forward and pressed open mouth kisses to Annie's lower stomach as he tugged her underwear off, depositing them on the floor as well. He then lay down on his stomach, maneuvering Annie's thighs over his shoulders as he pressed kisses to her inner thighs.   
"Jeff, you don't have to-" Annie gasped softly, her face flushed.   
"I'm going for spectacular Annie," Jeff reminded her with a smirk, looking up at her face.   
"No but, no one's ever..." She trailed off, and Jeff was reminded that yes, Annie had had sex, but probably not a lot. Had that been what she'd meant by him being more man than she was used to?   
"Well that's the thing about an older man Annie," He drawled, still smirking as he pressed a kiss to her hood. "Comes with the perk of experience," he purred, before he attached his mouth to her clit and lapped.   
Annie's back arched and her head fell back and the hottest sound Jeff had ever heard tumbled from her lips. He hummed against her, his tongue working on her like she would be his last meal. To be honest, he'd die happy if she was.   
"Fucking... Jeff," Annie whined.   
"I'm getting there baby," He chuckled softly as he came up for air, sliding a finger inside her as he reattached his mouth to her. She whimpered, her thighs clamping around his face a little. Again, being smothered by Annie wouldn't be the worst way to go.   
"Baby?" She breathed out curiously, an elated smile forming on her lips between moans. Oh so she liked the pet names? Figures, Annie would definitely be all about pet names.   
"Yeah, baby, you're my baby, my girl," He promised her between licks. He wasn't sure if now was the time to be making those sorts of promises, but eating Annie out was making him a little delirious, he was rutting his hips against the bed for friction forgodssakes. He'd never found eating a girl out so hot before, sure he'd been happy to do it as part of foreplay, but he'd never gotten so aroused by it.   
Annie seemed to be turned on by the promises though, if the increasing sounds of her moans were anything to go by. Jeff had three fingers in her now, and her hips were rocking against his face and his fingers. He curled them and Annie let out a shout. He must have found her sweet spot then, so he continued to stroke over it, giving it his undivided attention.   
"Jeff, now, c'mon, please, I can't hold off much longer," Annie whimpered out, her face a delicious shade of pink. Jeff let up, sliding up her body and kissing her deeply. He moaned as she eagerly kissed and licked at his mouth, tasting herself on his lips. She used the tips of her toes to slide his boxers down his legs.   
"Oh, look whose got skills?" He joked softly, kicking his boxers off his ankles once they were there. Annie wiggled her eyebrows at him with a giggle. Jeff reached across her into the nightstand, pulling out a condom and making quick work of sliding it on.   
God, he was about to be inside Annie Edison.   
"Hey, don't back out now," Annie murmured, obviously seeing the realisation on his face. "You're seconds away from spectacular," she smiled, leaning up so her lips brushed his earlobe, "Mr Winger," She finished, biting down on his earlobe gently.   
Jeff shuddered and that was all the convincing he needed. There was no way he could deny that name for the second time today. He lined himself up and slowly pushed in, moaning as her legs automatically wrapped around his waist. “God,” he breathed out, resting his forehead against hers. Their breath intermingled, their lips brushed weakly as Annie whimpered, adjusting to him. Jeff slid one hand under her back and lifted her a little to help her, and Annie moaned in appreciation. She was so warm and wet around him, Jeff could cry from how good it felt.   
“I’m good,” she breathed, nodding slowly. Jeff nodded too and kissed her again before sliding himself out and then slamming back in. Annie groaned against his lips, before her head automatically fell back against the pillow. Jeff kissed and nibbled at the exposed skin of her neck. He remembered her vampire story she’d told a few Halloween’s ago, and with that he bit down on the curve of her neck a little harder.   
“Jeff,” Annie moaned his name and Jeff sped up his thrusts. He braced his knees so her legs automatically gripped tighter around his middle. He then gripped one hand on the head board to give himself more leverage, sliding his free hand between them to thumb over her clit. Annie was moaning desperately between them, and Jeff’s loud panting joined her noises. They sounded so hot together.   
“Jeff,”   
“Annie,”   
“God,”   
“I know baby.”   
They’d always been able to finish what the other was thinking, and this was no exception. Jeff could feel Annie’s thighs trembling, but the rest of her body was going rigid. She moaned his name as she came, her back arching off the bed, smothering Jeff’s face with her breasts. He didn’t mind, he latched his lips to one nipple and sucked on it as her orgasm powered through her. She whimpered weakly and gripped his biceps. His thrusts were getting sloppy as his own orgasm was building, and she was trembling from sensitivity. She wrapped her arms around his neck, bringing their faces back together in a kiss.   
“Fill me up Mr Winger,” she purred.   
“Christ, Annie,” he gasped out as he came, his hips stilling and his hand finding purchase on her thigh, gripping tightly. His whole body shivered as it rocked through him, his chest rising and falling in heavy pants as he came back down to Earth. He gently pulled out from her and rolled on the bed beside her, dumping the condom in the bin beside his bed, before wrapping one arm around her and resting it on her hip.   
“You’ve got a filthy mouth Annie,” he panted softly, a dazed smile on his lips that matched Annie’s.   
“You bring it out of me,” she hummed.   
“Somehow I don’t think that’s true, you seemed to know exactly what you were doing,” he chuckled.   
“I just know you,” she murmured, rolling her head to connect their eyes. Jeff smiled back at her and inched forward to kiss her sweetly. “You okay?” She asked.   
“I should be asking you that,” he said, stroking circles on her hip.   
“I’m fine,” she promised.   
“Only fine?”   
“I’m spectacular,” she giggled, rolling her eyes fondly.   
“That’s better,” he chuckled. “I’m spectacular too, I’m sorry it took so long for us to do that.”   
“Ah well, you’ve learned your lesson, we could have been doing that the whole time and now you’ll have to regret it whenever it's that amazing,” she teased.   
“I’m sure I can make up for lost time,” he whispered, kissing her cheek. His eyes were slowly slipping shut - Sue him, he was 40, and that had been a lot of effort on his part.   
“I should get home Jeff,” Annie whispered. Jeff pouted and squeezed her hip.   
“You’re not going anywhere, grab a shirt and get comfortable,” he croaked tiredly, not even opening his eyes. If he had, he might have seen the incredibly happy smile on Annie’s face as she grabbed one of his shirts from the drawers, and cuddled up against his chest.

Jeff woke up to the smell of something sweet. His eyes slowly opened and he looked down and saw a pillow in his arms. He’d been drooling so he was thankful it wasn’t Annie’s actual head. It smelled like her a little, but that wasn’t the sweet thing he smelled. He climbed out of bed and pulled some fresh boxers on, walking out of the room and seeing Annie in his kitchen. Her hair looked slightly damp so she must have taken a shower, but she was still wearing his Greendale t-shirt the Dean had insisted he have. It was tight on him (which he knew had been the Dean’s intentions), but it still fell to Annie’s mid thigh. She was humming a tune and the smell was the pancakes she was making. “I didn’t know I had ingredients for pancakes,” Jeff croaked, voice thick with sleep as he leaned on the doorway of the kitchen.   
Annie turned to face him, her eyes unashamedly looking his nearly naked form up and down.   
“They’re healthier than I’d usually make them, I used mostly bananas,” she chuckled. Jeff’s heart was thrumming from how beautiful she was, standing here in his kitchen, wearing his clothes, cooking them breakfast. He’d never had anything even as somewhat domestic as this before. She must have noticed him staring, because she began playing with the hem of the shirt.   
“Britta told me you don’t let the girls you sleep with borrow your clothes, so I hope this is okay,” She said timidly. Jeff cursed Britta in his head yet again for making Annie doubt how Jeff felt about her.   
“You need to stop listening to Britta,” he said, slowly walking towards her. “You’re not just a girl I’m sleeping with, you’re...” he trailed off, nerves getting the better of him. “And besides, as if I’d let Britta wear any of my clothes, she’d get them dirty in two seconds,” he chuckled. She chuckled along as well, looking shyly up at him. “And you look so cute and hot in my clothes, the only alternative that would be better would be no clothes,” he added. Annie rolled her eyes fondly, stroking over his bare chest.   
“What were you going to say?” She whispered. “I’m not just a girl you’re sleeping with, what am I?”   
Damn, Jeff knew she wouldn’t let him get away with it. He’d said it last night, but saying it in the light of the morning without the atmosphere of sex to cover for him made him feel so much more vulnerable.   
“Well, you’re Annie, you’re a girl I really care about, you’re...” he trailed off again then took a deep breath and met her big blue eyes. “You’re my girl, if that’s what you want to be,” He finished.   
Her smile was so wide it nearly split her face in two. All she could do was nod, before leaning up and kissing him deeply. “And you’re mine?” She asked softly.   
“I’m your girl,” he joked. Annie laughed, resting her face against his chest as they held each other.   
“Good,” she breathed, pressing a soft kiss between his pecs. He held her close, he knew she must be able to hear his heart thumping in his chest.   
“The pancakes are burning,” she murmured when she tried to pull out of his hold. He didn’t let her go.   
“Let them,” he murmured, kissing the top of her head.

**Notes for the Chapter:**

> Hope you enjoyed it! I'm toying around with the idea of a third chapter where they sneak around for a bit before telling the group, but I'm not sure if I'll write that as part of this fic or a new fic all together. Rest assured this won't be the last you read of Jeff and Annie from me. Thank you again for the loveliness for this fic. Keep safe with everything going on, look after each other, and I hope this story brought you joy in a time where there isn't a lot to go around <3


	3. Chapter 3

Jeff was awoken by the sound of a soft thud hitting his bedroom floor. He cracked one eye open and saw Annie leaning down to pick up her school book she had just dropped, quickly pushing it into her bag. She was wearing one of her business skirts with tights, and a tucked in blouse. Gone were the days of Annie and her brightly coloured skirts and cardigans. Jeff did miss those sometimes, but he knew Annie was getting older and wanted to dress more like it. Besides, when she was bent over like that the tight business skirt didn't leave a lot to the imagination. Jeff glanced at the clock on his bedside and saw it was only 7:30 in the morning.   
He scooted the upper half of his body off the bed and wrapped one arm around Annie, pulling her back into bed. She squealed as her head hit the pillow, Jeff leaning over the top of her.   
"And where do you think you're going?" He hummed, his voice thick and slightly deeper.   
"Back home, Abed and Troy will be waking up soon," She pointed out, stroking over his bare chest. "They already question why I have to leave the apartment to 'study', can't let them figure out that I'm actually staying the night at some old guys apartment," She smirked.   
"Oh I'm just some old guy?" He asked with a chuckle. "If you're not careful I'll never let you leave."   
"Yes you will, otherwise they'll figure it out," She said, raising an eyebrow at him. "I could stay over more often and sleep in if we just told them," She sighed. Jeff licked his lips. He knew Annie wanted to tell the group, but he also knew they both agreed it probably wouldn't go well.   
"Annie they'll kill me, and they'll lecture you and treat you like a child," He repeated, he'd said the same thing a week ago.   
"I know," She agreed, she always did.   
"Just a little longer baby, this past month together has been perfect, I don't want them to pop our bubble too soon," Jeff stroked her hair while he spoke, then pressed a kiss to her cheek. "Trust me, I can't wait for the days where we're only waking up at 7:30 to squeeze in a round before class," he joked softly, pinching her side. She laughed and leaned up to kiss him. Jeff hadn't ever dated someone for this long and still been so excited and somewhat addicted to the kissing part. He and Annie had amazing sex, there was no denying that, but Jeff found himself prolonging the making out more than he usually would because he just adored kissing her. Her lips were so soft and he could hear the little content sounds she'd make sometimes and he could feel how small she was in his arms.   
"I have to go," she whispered against his lips, pulling him from his reverie.   
"If you wear that skirt to school I can't be held accountable for the amount of times I'm going to pull you into an empty classroom," He hummed back.   
"All the more reason to wear it," She smiled innocently, kissing him once more then sliding out from under him. Jeff watched her straighten her clothes back out, smirking when she hitched the skirt just a little higher than it had been before. He watched her then gather up her clothes from the day before.   
"Is there anything I can wear that gives you the same reaction your skirts give me?" He asked curiously.   
"Your cowboy costume from our first Halloween," Annie answered quickly. She blushed a little and smiled to herself. Jeff raised an eyebrow with a cocky smile plastered on his face. "I'll see you at school Jeff," She squeaked before quickly leaving the room, and moments later he heard the front door to his apartment shut. 

When Jeff arrived to Greendale, Annie was already sat at the study table with Abed and Troy. He took a seat in his usual spot, and watched Annie talk animatedly about her criminology assignment. She'd already told him all about it the night before, so Jeff let his mind wander as he gazed at her. She was so cute when she got excited about things like this. He knew that criminology and forensics was definitely her passion, way more than hospital administration ever had been. He didn't even really notice Britta and Shirley arrive.   
"You look happy today Jeff," Shirley chirped with a smile. Jeff glanced over at her and realised he was wearing his stupid fond smile he seemed to always have for Annie when she was being particularly cute.   
"Happy it's Friday," Jeff shrugged her off, quickly looking down at his phone.   
"Oh big plans for the weekend Winger? What's her name?" Britta raised an eyebrow at him. Britta had been the only one in the group they'd struggled to get off the scent. It hadn't taken much for Troy and Abed to believe that Annie went back to Greendale at night sometimes to study - it was something she'd do and Annie was usually very truthful with them so they had no reason to believe she was lying. Shirley and Hickey had no idea anything was going on, but Annie had gone to Britta for advice about Jeff. Annie had told Britta she'd backed out and never done it, and Jeff had been pretending to be sleeping around a lot on the weekends.   
"Don't know yet," Jeff shrugged noncommittally.   
"Pig," Britta rolled her eyes.   
"OH MY GOD ANNIE WHAT IS THAT?" Shirley suddenly shouted. Annie quickly put her phone down, her face bright pink and her eyes wide.   
"Nothing," She squeaked. Jeff frowned, confused.   
"Annie who is sending you pictures of their penis?" Shirley gasped.   
"What!?" The whole group shouted, except Jeff, who had a sinking feeling in his stomach. Annie hadn't been able to come over last week because Troy needed help comforting Abed over some Inspector Spacetime thing - Jeff hadn't really paid attention to that part because Annie had sent him some naughty texts instead. It had gone quite far, and he was assuming that's what Shirley had just seen.   
"Annie are you getting unsolicited dick pictures! That's so incredibly misogynistic, who is this guy?" Britta snapped, her arms crossed.   
"He's nobody, some guy I was talking to, when people text me pictures they automatically save in my phone," Annie quickly lied with a groan, covering her face. At that moment Troy took the opportunity to swipe Annie's phone.   
"Troy! No!" Jeff shouted.   
"Oh my god!" Troy gasped when he saw the picture.   
"Troy give it back!" Annie growled, marching over to him.   
"Everyone needs to see it now, that would be the way this sequence would go," Abed pointed out, looking over Troy's shoulder at the picture. "Interesting," He said.   
"This is not an episode of some show, this is my privacy, give it back!" Annie yelled, taking it off Troy.   
"Oh so I don't get to see it?" Britta cried.   
"Why do you want to see it?" Annie asked.   
"Sequencing or whatever," Britta shrugged, not meeting her eyes. Jeff was still sat in silence from shock, his heart racing. He couldn't believe practically the whole study group just saw his god damn penis. And Britta had seen it before, so that meant everyone had indeed seen his penis now at one point or another.   
"Annie do we need to talk to you about who you talk to on the internet?" Shirley asked kindly, turning to face Annie.   
"No, I'm fine, I'm capable of deciding who I talk to," Annie sighed, putting her phone away.   
"Jeff! You've got some weird protective dad thing over Annie, say something!" Britta interjected, looking at him expectantly. Jeff sighed.   
"Annie can do what she wants, she's an adult," He said.   
"Thank you Jeff," Annie nodded, crossing her arms, although she wasn't quite meeting his eyes. "Can we just talk about something else?" She pleaded.   
The room went silent.   
"Wait, Annie, are you allowed to sleep with someone who isn't circumcised?" Troy asked.   
"I have to get to class," Jeff groaned, getting up and storming out. 

Jeff didn't see Annie for most of the morning, which was a shame because he really did like her in that skirt. And he missed her.   
Around lunchtime, Annie came to Jeff's office before they were due to head to the cafeteria to see the rest of the study group.   
"Hey," She murmured when she opened the door, glancing around to check for Hickey. She shut the door behind her when she came in. "Jeff, I am so so sorry. I was going through my photos to find some notes I'd taken a picture of, Shirley must have seen it over my shoulder," Annie apologised, walking over to him.   
"Annie it's okay," Jeff sighed, sitting on the edge of his desk and pulling her between his legs to hold her hips. "I mean, I would prefer if the entire study group didn't know what my penis looks like, but it was an accident," he couldn't help but smile a little.   
And then they were laughing.   
Full belly laughter that soon turned into a tender kiss.   
"God, good thing Britta didn't see it, we would have been busted," Jeff chuckled when they pulled apart.   
"What? You think she would remember it that well?" Annie asked, raising an eyebrow.   
"Are you saying my penis isn't memorable?" Jeff teased, pinching her bum. She squeaked and then giggled.   
"Course not," She rolled her eyes. Annie pecked his lips one more time then the two began walking to the cafeteria. Jeff found it hard to not hold her hand when they walked together. It felt so instinctual, he wanted the world to know who he was dating. Of course, now when they told the group, the group would all know who that picture had belonged to, but Jeff wasn't as worried anymore. He and Annie could get through it, and he'd be able to hold her hand, and kiss her at her locker, and wake up next to her at normal hours of the morning. Maybe the time to tell them would be sooner than he'd thought. 

When they reached the cafeteria it would seem the topic of the penis photo was old news. The group was now discussing the first dance of the semester, which would be in two weeks. The theme was 1920's and the group was discussing whether or not that was the theme purely so the Dean could wear a feather boa.   
"Annie!" A voice from behind Jeff called out. He turned and saw a young guy with dark hair and the sharpest jawline he'd ever seen walk towards them.   
"Hey Trev," Annie smiled, standing up to talk to him. "How did your test go?" She asked.   
"All the better thanks to your notes, you're amazing," This Trev guy gushed.   
"Maybe he's the guy who sent her the picture," Troy whispered to Britta, loud enough that everyone else at the table could hear. Even though Jeff knew that wasn't the case, something irrational began to claw from within him. This irrational beast was angered even further when Shirley murmured, "Well maybe that's not so bad, he's gorgeous."  
"Annie," Jeff said, unsure if he'd interrupted them and honestly, uncaring if he had. "Introduce us to your friend," he tried not to sound icy, he wasn't sure if he succeeded.   
"Oh, sorry, guys this is Trevor, he's in one of my Forensics classes, Trev these are my friends," She smiled brightly at this guy. This douche bag wearing the tightest jeans Jeff had ever seen and the hint of a tattoo on his bicep peeking out from his sleeve. Jeff didn't like him.   
"Trevor, do you usually rely on young girls for study notes?" Jeff asked, cocking his head.   
"Jeff!" Annie frowned. "I was happy to help," she assured Trevor.   
"I'm glad, I know you offered but I would feel so bad if you thought I'd just relied on you instead of working it out myself," Trevor said to Annie, before turning to Jeff. "Also what are you talking about young? Annie and I are the same age," He chuckled, still somehow sounding polite and charming even though it felt like he was stabbing Jeff with a knife.   
"And Jeff, you're the one who relies on Annie for notes," Britta pointed out.   
"And you're old," Shirley added.   
"Yeah but... that's different, we're friends," Jeff stammered.  
"You look great for your age man," Trevor smiled, obviously trying to be polite but just succeeding in making Jeff want to punch him. "Annie has talked about all of you a lot, it's so nice to finally meet you and I wish I could get to know you all more but I've got to run."   
"Oh, such a shame," Jeff muttered, and Britta kicked his shin under the table.   
"Rude," She mouthed, making Jeff roll his eyes.   
"I'll see you later right Annie?" Trevor murmured to her, and the beast inside Jeff made him watch as Trevor squeezed her arm then pulled her in for a hug.   
"Oh, yeah, see you," Annie smiled, her face flushing a little in the hug before Trevor pulled back, smiled widely at her and left. Annie took a seat across from Jeff, who must have been staring at her somewhat angrily. "What?" She asked.   
"Protective dad thing," Britta elbowed Jeff in the side. He winced but didn't deny it.   
"He seems nice Annie, very handsome," Shirley cooed across at her.   
"Oh so when he's handsome it's alright for him to send her pictures of his penis?" Jeff ridiculed.   
"He didn't send me anything," Annie reassured the group, giving Jeff a look.   
"Oh, well he's even better then," Shirley smiled wide and Jeff internally groaned, he'd walked himself into that one.   
"He's just a friend," Annie stated, though her face was still flushed and she was fiddling with her hair a little. The beast inside Jeff was clawing to get out, grab Annie and make out with her right here on this table to prove a point. He clenched his fist.   
"His jeans were so tight," Jeff pointed out. "You really wanna sleep with someone who allows that sort of treatment on his genitals?"   
"Oh please Jeff," Britta rolled her eyes before Annie could get a word in. "Just because you couldn't pull those jeans off anymore," She chuckled, and the group snorted and agreed with her.   
"I don't need this kind of mockery, I could pull off skinny jeans any day I liked, but I wouldn't want to ruin the life of every guy at this school," He said petulantly, standing up and grabbing his books and leaving the cafeteria. He could totally wear skinny jeans, he'd show them. 

So they didn't fit. Jeff tugged and pulled and contorted his body every which way, almost falling over his desk chair as he tried to pull these stupid skinny jeans higher up his legs. He'd managed to fit the button up shirt on, it was tight around his muscles but at least that was flattering. The cowboy hat was sitting on the desk as well as the belt, but he couldn't get the stupid jeans on that went with this costume. He'd only worn this a few years ago, had his body changed that much since then?   
Just as he managed a little bit of give, the door to his office opened. It was after 4 so he'd assumed Hickey (and pretty much all Greendale students) had gone home. He began blabbering out for whoever it was to stay out, but when he looked up it was Annie standing in the doorway, looking very confused.   
"What are you doing?" She asked, slight laughter in her voice. This was supposed to be sexy, not funny.   
"I was going to come pick you up and surprise you in the cowboy costume," Jeff explained, a slight breathlessness to his voice from trying to get the jeans on. "But these stupid things won't come up, they must have shrunk in the washing machine," he lied. Jeans never shrunk this much. Annie giggled a little.   
"You keep the cowboy costume at school?" She asked.   
"It was in my car," He replied, giving up and kicking the jeans off, leaving himself just in his boxers and the shirt. He took a seat at his desk with a huff, putting the cowboy hat on with mock jazz hands. "Ta da," He said sarcastically.   
Annie bit her bottom lip and closed the door behind her as she came in. "I don't think we need the jeans for this anyway," She smiled, slowly walking towards the desk. Jeff raised an eyebrow. Maybe this had had the desired effect, skinny jeans be damned. And doing this right here in his office was even hotter than the plan of just doing it at his place.   
Annie came round the other side of his desk and Jeff rotated the chair to face her, patting his thighs.   
"Ready to ride baby doll?" He smirked, putting on a southern drawl with a wink. Annie climbed into his lap so she was straddling him, taking the hat off his head and putting it atop her own head.   
"Show me what you've got cowboy," She breathed, grabbing his collar and kissing him. 

They didn't talk about Trevor. Throughout the following week, whenever Annie had a forensics class before lunch, Trevor would walk her to her table ("Like a gentleman," Shirley had giggled), greet the group with that too-charming smile and hug her goodbye. Every time, Annie would giggle at the study group's lighthearted teasing and twirl her hair. It reminded him of years ago when she'd dated Vaughn, she'd seemed so young then and it made her seem younger now, which only made Jeff's beast, as he'd come to know it, angrier.   
Every time he so much as saw Trevor walking with Annie in the hall, he'd find an excuse to get her alone later, prove to her that he could still do the young and hot thing. They'd made out in empty classrooms, he'd eaten her out in his car in the Greendale parking lot, they'd even had sex in the study room late one day after everyone had left (Annie had claimed victory when Jeff had promised that time had been better than his time with Britta, and Jeff wondered briefly if Annie had her own beast, maybe hers could be friends with his).   
Jeff could practically hear 'Psychologist Britta' telling him this wasn't healthy. He should talk to Annie, tell her how he was feeling. But the self-destructive part of him was enjoying the slightly more possessive sex, even if it exhausted him to the point where he was napping between classes. Which only made him feel worse about his age, which made him angrier when he saw Trevor, and the vicious cycle started all over again.   
It all built and collided two days before the dance. Annie and Jeff had gotten to the study room early under the pretense of working on Jeff's curriculum, but instead they'd made out for a while and had breakfast together.   
"So, are we going to the dance together on Friday?" Annie asked as they actually began to open up Jeff's books to work on his curriculum. Jeff raised an eyebrow at her.   
"I don't see why we would, it's just a dance right? We'll all hang out there together anyway," Jeff replied, under the impression they were still agreeing to hide their relationship. Annie pursed her lips.   
"Okay well... Trev asked me to go with him," She said, fiddling with the strap of her bag. The beast inside Jeff roared and Jeff clenched his fist under the table.   
"You haven't told him you have a boyfriend?" He asked stiffly.   
"Well it would be as friends," Annie explained.   
Jeff didn't think Trevor meant it as friends, but what else was he supposed to say? He didn't want to be the asshole boyfriend who told Annie who she could and couldn't hang out with. "If you want to go with him, fine, go with him," he muttered against his better instincts. There was a beat of silence.   
"So it doesn't bother you?" She asked.   
"Nope," He lied, popping the 'p', of course it did. It extremely bothered him and the beast was banging against his ribcage, fighting against the words coming out of Jeff's mouth. He didn't want to have a fight with Annie, so if he just let her do what she wanted, everything would be fine.   
Except it wasn't.   
"You'd rather let me go to a dance with someone else than just admit you're jealous and let us tell our friends?" She snapped.   
"I'm not jealous," Jeff instinctively shot back.   
"Oh come on Jeff," Annie rolled her eyes, slamming her book shut. "How stupid and naive do you think I am? You think I don't know what all these little secret sex sessions have been about? You think I don't notice that they're all conveniently after whenever you see me with Trevor? Or whenever anyone talks about him?" She cried.   
"You think I don't notice you blushing and twirling your hair whenever he's brought up?" Jeff argued.   
"Jeff up until the last few years guys have never been interested in me, it makes me flustered okay? It doesn't mean I'm interested in him, it's just a reaction to being hit on," She explained. "And don't change this back on me! You just agreed to me going to a dance with some other guy just so we don't have to tell our friends!"   
"They'll ruin this! I don't want us to be ruined!" Jeff yelled back. He didn't want to fight with Annie. He refused to let his voice crack or his eyes tear up, he never cried in front of anyone, but it made him realise exactly how hard he'd fallen for Annie if it was affecting him this much.   
"Will they? Or are you just scared you'll ruin us and telling them makes that too real for you?" Annie hissed.   
"There's an us?" A voice from the doorway of the study room cut them both off. Jeff didn't need to look to know who was there, the look of surprise and horror on Annie's face gave it away. Nevertheless, he slowly turned in his chair to look at the door, and saw all their friends standing there, absolute shock clear on all their faces, even Abed's.   
"How long have you two been an us?" Britta had asked the first time, and it was her who spoke up again. Jeff swallowed thickly. Everything was crumbling down.   
"A little over a month," Annie breathed, standing up and gathering her things.   
"Where are you going?" Jeff asked quietly.   
"I wanted to tell them ages ago, no matter how they reacted, you made this mess, you lie in it," She sighed, and Jeff could see her eyes were wet. He was honestly a little surprised she'd been able to hold her tears in for so long. "I need space," She murmured.   
Jeff did not like the sound of that.   
"Annie, please," He began, but she was already marching out of the study room. Jeff could feel all the eyes of his friends on him, but it didn't matter if the blue eyes he'd fallen in love with couldn't even look at him. 

Jeff took two sick days off work so he didn't have to be at Greendale. He couldn't face his friends, who all had looked at him like he was scum of the Earth before he'd marched out of the study room moments after Annie. He'd lost his girlfriend and his friends all in five minutes and he could only blame himself.   
Annie had been right. Of course she had been. The excuse of not telling their friends because of their reaction had been a lie, one he'd even believed himself. The truth was the moment they told their friends, that was when their relationship would feel the most real, that was when Jeff officially had the chance to ruin it.   
He'd decided all of this was probably for the best. Annie deserved better if this was how he behaved in a relationship. Jeff Winger wasn't made for the long term, and he'd given into that after a few glasses of Scotch, sitting in front of his TV, pathetically holding one of Annie's cardigans she'd left at his place.   
His pity party was interrupted when there was a knock at his apartment door. He wiped his face and set the cardigan down on the back of his couch as he got up to answer it. Probably the pizza he'd ordered - that's how he knew this must be heart break, he was willingly eating pizza all to himself.   
But it wasn't his pizza, or, well it was, but the delivery guy looked an awful lot like his study group.   
"We saw the pizza guy downstairs, figured we could just deliver it," Abed said, handing Jeff the pizza. He, Troy, Shirley and Britta all filed into his apartment. They were all dressed quite dapper and Jeff realised they must be on their way to the 1920's dance.   
"You guys here to murder me on your way to the dance?" Jeff asked.   
"We discussed it," Britta said.   
"But it looks like you've already begun to murder yourself," Troy remarked, looking at Jeff's scruffy appearance, the Scotch bottle on the table, before his eyes finally landed on Annie's cardigan. "Annie's been here?" Troy asked.   
"She left that here last time she was over," Jeff muttered.   
"So she's been coming here, not studying at Greendale late?" Abed asked. Jeff nodded.   
"She's been...staying the night?" Shirley asked slowly, eyes narrowing a little. Jeff rubbed his face just as she gasped. "Oh my god that picture!" She cried.   
"What do you guys want?" Jeff asked bluntly, cutting to the chase.   
"To tell you to go to that dance and win Annie back," Britta answered.   
"Like in the climax of a romantic comedy, except without having to beat the plane taking off trope, you just have to profess your feelings at a dance. It's very disappointing for me," Abed stated.   
"I'm not professing anything, she wants space, and that Trevor guy can probably give her a lot more than I can," He said, crossing his arms. "Besides, I thought you guys would be against us," He pointed out.   
"We don't love the idea," Shirley admitted.   
"But we also haven't given you guys a chance, which isn't fair," Troy added. "You guys all gave Britta and I a chance, you and Annie deserve that too, even if it's grosser."   
"The age difference is basically the same - oh whatever," Jeff groaned. "So you guys... give me your blessing?" He asked.   
"Reluctantly," Britta smiled up at him, "but yeah."   
"So long as you don't hurt her, or we'll all destroy you," Abed said firmly. Jeff met Abed's eyes. Abed, the guy who wasn't usually passionate, or emotional, had just threatened him. Jeff knew it wasn't an empty threat either. Anyone could tell Abed treasured Annie's friendship, especially since they'd moved in together, they were like brother and sister, and Annie was probably second only to Troy.   
"I've already hurt her," Jeff sighed.   
"Not completely, yeah you were a jealous idiot who didn't tell her how he was feeling, but that's got to be old Jeff Winger now, if you want to be with Annie, that has to stop, and you've got to promise her it will," Shirley said firmly. "Isn't she worth that?" She pointed out.   
Jeff swallowed thickly. Annie was worth everything. The scary thing was he'd give up all he had in a heartbeat if it meant being with her. He knew he was desperately in love with her, and it was terrifying.   
And yet every part of Jeff was telling him to risk it anyway.   
"Go get dressed, shave, put on the Winger charm, and lets montage it all," Abed said firmly. Jeff didn't need to be told twice. 

He'd pulled on his best suit, a dark navy one, shaved, styled his hair and sprayed on Annie's favourite cologne, all while Abed played 'montage music' from his phone. He couldn't deny, it did make him feel like he could do anything. Even win back a girl he totally didn't deserve.   
The nerves erupted in his stomach when he pulled up to Greendale. The others had already gone inside, Jeff had watched them walk in. He didn't want Annie to feel ambushed. He took a few deep breaths before climbing out of the car and going inside himself.   
He knew Annie had been helping set up the dance over the week, and she'd done an amazing job as always. There was beautiful lights hanging everywhere, 1920's jazz music playing and plates of food that looked like it was clear crystal but Jeff figured Annie would be smart enough to just get plastic, not real crystal, for a Greendale dance.   
It was a good turn out, and Jeff's eyes landed on his study group all dancing in the middle with Annie - and Trevor.   
Jeff expected the beast to show its anger, and it did, but it was more of a dull growl, because it was overshadowed by his own guilt. He'd done this. He'd pushed Annie into some other guys arms.   
But he was here to get her back, and nothing would get in the way of that. Annie would like a big grand gesture, he was sure of it. His girlfriend - hopefully still his girlfriend - was a hopeless romantic, who fell for charms and declarations.   
Fortunately, Jeff had a way with words.   
Jeff walked across the room towards the small stage, where the Dean was standing in a black, sequinned flapper dress and, indeed a bright pink feather boa wrapped around his neck.   
"Jeffrey, come to sweep me off my feet?" The Dean smiled, fluttering his eyelashes.   
"Here to sweep somebody off their feet, where's a microphone for the sound system?" Jeff asked, sidestepping the flirting.   
"Jeffrey we haven't had a microphone at a dance since Britta and Slater professed their love to you - Oh God are you about to do that? I'll find you one right away," The Dean beamed, obviously thinking Jeff was going to do that for him, before scurrying off to find one backstage. He reemerged with a glittery one. "This one was from Glee Club's last performance but it'll do," The Dean smiled, handing it to him. Whilst usually Jeff wouldn't want to touch anything associated with Glee Club, he'd do anything for Annie. He grabbed the microphone and switched it on, the feedback cutting through the music making the whole crowd groan and turn to look at him.   
Immediately, his eyes found Annie's, who was looking at him with a mix of confusion and slight annoyance.   
"Good evening Greendale, you're all uh... looking very dapper," Jeff began.   
"Oh Jeffrey, you charmer," The Dean gushed beside him and Jeff took a few steps away from him. Hopefully he'd take the hint, he usually didn't.   
"I'm up here to use my words to make a grand gesture, to profess my feelings which I'm usually not very good at but... well I need to be good at it now," Jeff stumbled over his words. Dammit his Winger speeches were usually the stuff of legends, this was barely worth a watch. He looked at his friends who, bless them, were actually giving him reassuring looks. Maybe he'd doubted them and their reactions, maybe in the end they just wanted to see both himself and Annie happy.   
Jeff had been such a fool.   
"Annie I'm a fool," He voiced his thoughts. He reconnected their eyes again and was glad to see the annoyance had dimmed from his confession. He was on the right track. "I'm such a fool, I thought spending any day not showing you off was a good idea, I thought not holding your hand in the hallway was better for us, I thought hiding you and how happy you make me would be healthy," He swallowed thickly. "But Annie I'm a fool for you," He breathed. The whole room gasped.   
"Aren't you like twice her age?" Someone, Vicki, he thought, shouted.   
"Yes," Jeff answered. "And I'm a fool because I thought that mattered," He decided to stick with the fool motif, it seemed to be doing wonders for him if Annie's fond look was anything to go by. He was walking closer to her, close enough for them to touch. He passed the microphone to Abed, who was now filming all of this for some reason, and kept the microphone close to their mouths anyway. "Annie I'm such a fool, I'd let myself be jealous and petty before admitting that I'm afraid I'll be so bad at this and lose you," He said to her, taking her hand gently. "I don't deserve you, in more ways than one, but I want to do everything I can to make up for all this, to be deserving of you. I want to hold your hand everywhere we go, I want to kiss you at your locker, I want to sleep in with you and come to school together, God, baby if you want to fulfill your holding hands at Disneyland fantasy, tell me and I'll book the flights tonight," He smiled, basically beaming when she giggled back. He could die happy listening to her giggle. He had to tell her that.   
"I love you Annie," came out instead.   
Annie gasped, along with the whole study group. Maybe they hadn't had expected as much from him as he'd briefly thought they had.   
He didn't care, he was too busy looking at Annie, gauging her reaction.   
"You didn't need to say all that in front of everyone," She whispered.   
"You loved it," Jeff remarked softly with a smirk.   
"Not as much as I love you," She hummed, biting her bottom lip. "I was a fool too... I let the Trevor thing go too far, I should have talked to you about it," She said. "From now on, we talk, we don't get jealous of past exes or not even potentials," She added, obviously hinting about her worry of Britta, which Jeff appreciated. For them to be healthy, they both needed to address their insecurities.   
"Can I finish my grand gesture now?" Jeff grinned. Annie giggled and nodded. Jeff scooped her up and kissed her deeply, spinning her around. He wasn't expecting applause or anything, this wasn't an actual Disney movie, but the Dean screaming out "No!" would have to do.   
The music came back on when Abed turned the microphone off. Jeff put Annie down, the two smiling against each other's mouths. He rubbed her back and the two looked at the group, who were wearing mixed expressions of reluctance and happiness for them.   
"Abed why are you still filming?" Jeff asked.   
"The perfect ending to my rom com Jeff!" Abed explained.   
"You haven't filmed us doing anything else for a movie though," Annie pointed out.   
"You're a generic looking white couple, I can find actors who look close enough," Abed shrugged.   
"Wait, so, Jeff... that picture was photoshopped right?" Troy asked.   
"Oh God," Jeff groaned and turned back to Annie. "Care to dance away from all this Milady?"   
"With pleasure Milord," Annie agreed, hanging onto him as they twirled away. It didn't stop their friends from following, Abed leading the pack with his camera.

**Notes for the Chapter:**

> There you have it! This fic turned out to being so much bigger than I thought it would be. What started as a one shot turned into three chapters, and I'm still going to add in a 'alternate timeline' chapter that shows what would have happened if Jeff had given in in the office in the first chapter... so stay tuned!   
> But the love for this fic has been so so nice for me to read, I really appreciate it, and it has definitely made me want to keep writing Annie/Jeff. I've got a lot of ideas, and please feel free to comment any fic ideas you wish were being written - I know there isn't a huge amount of Jeff/Annie out there, but I always welcome ideas.   
> Thank you again, see you soon!


	4. The Alternate Timeline

**Notes for the Chapter:**

> This is basically just chapter one but in an alternate timeline - what would have happened if Jeff hadn't denied Annie's advances. Very smutty, obviously. Enjoy!

"Come in?" Jeff called, obviously surprised because Greendale students didn't usually knock.   
Annie swung the door open slowly, biting back her smug smile when she saw Jeff's eyes widen, very obviously looking her up and down from where he was standing next to his desk.   
"Can I talk to you for a second Mr Winger?" Annie asked, her voice taking on a slightly higher pitch that she'd used on Jeff before.  
Jeff lost his grip on the papers he'd been about to pick up, the stack fluttering to the ground, but Jeff didn't take his eyes off Annie.   
"Oopsies," she giggled, rushing forward and bending down with her ass remaining in the air to scoop up the papers. Sure, it was cliche, but a school girl kink was pretty cliche in the first place.   
"What... Annie what are you doing?" Jeff seemed to find his voice, though it was breathier than usual.   
"I came to talk to you about the first paper for intro to law," She smiled sweetly, handing him his papers and fluttering her eyelashes. "Unless you're busy, I can come back later Mr Winger," she added, biting her bottom lip a little.   
"Annie, Christ," Jeff breathed, shamelessly looking her up and down again. He quickly moved behind his desk, seeming to think a bit of space between them would help his cause. It didn't, Annie perched herself on the edge of his desk, her skirt riding up a little higher and fanning onto the wood.   
"I just wanted to make sure it's okay that I'm in your class now," Annie continued on, fiddling with a pencil on his desk, stroking over it with slight insinuation. Okay so she'd watched a few schoolgirl porno's when she got home. Whatever, it was research. "I'd hate to be a bother for you," she smiled, flicking her eyes up to meet his.   
Jeff still seemed a little stunned. "It's not a bother, Miss Edison," he finally spoke, his voice taking on a slightly deeper drawl as his hands slid into his pockets. "I only hope you'll be able to keep up with the work," he said, eyebrows raising almost in challenge. Annie steeled her gaze, then let out another girly giggle.   
"Well you could always be my private tutor if I get lost can't you?" She asked, cocking her head to the side. Jeff pursed his lips, slowly stepping back around his desk to stand in front of Annie. Annie turned her body so she was sitting completely on the desk, legs only slightly open in invitation.   
"This is a dangerous game you're playing Annie," Jeff said under his breath. It was a warning, Annie heard it as one. He was losing his resolve, he was letting her know he wouldn't be able to hold back much longer.   
Annie wasn't nervous, she wanted this. Despite being dressed as a schoolgirl, she'd never felt more mature in her life. She'd gone after what she wanted, and she wanted Jeff.   
The fact that he seemed to finally be understanding that, made her feel even hotter.   
"I understand, sir," she smirked. The sir seemed to have been the final straw. Jeff walked forward, hands finding Annie's knees. Annie automatically parted them more, using the heels of her feet to pull him between them. Jeff's hands slid up her thighs, finding purchase on her hips.   
"You look..." he struggled to find the words, "indescribable," he breathed with a small chuckle.   
"You like it?" Annie hummed, daring to lean forward a little and press small, soft kisses to the curve of Jeff's neck. Small steps, she'd learned. A full on mouth kiss might scare him off, the idea was to get him to initiate it.   
"I both like it and hate that other people saw you in it," He confessed, squeezing her hips. Possessive. Well that wasn't new, Jeff was always protective of her, it was only natural for possession to blur into that as well. It made Annie's cheeks heat up, the pink spreading down her neck to her breasts that were nearly spilling out of her shirt. The push up bra had been a good choice.   
"Don't worry, I'll only wear it for you from now on Mr Winger," She reassured, her hands sliding up his toned stomach and resting on his chest. He was so strong, so firm against her hands. So much taller, bigger than her. It was so attractive. She pulled her lips back from his skin, meeting his eyes briefly before he connected their mouths urgently. She moaned into the kiss, sliding her hands up over his shoulders to tangle in the ends of his hair. Her heart was beating like a drum in her chest and she wondered if Jeff could hear it, feel it. Every touch of his hands felt like electricity, tracing her skin through her clothes. His hands moved from her hips to slide down onto the desk, caging her in and gently pushing her onto her back so she was lying flat on the desk. Annie instinctively wrapped her legs around his waist, her mind racing with 'yes, yes, finally, yes.'   
Jeff kept one hand tight on her hip to keep her steady, as her lower half was off the desk, her legs wrapped around him and his hand the only thing keeping her up. He used his free hand to slide up her side, stopping to squeeze her bum, making Annie squeak. He then began to unbutton Annie's shirt with the one hand and Annie couldn't help but be impressed. Impressed, but also slightly terrified in remembering that Jeff had had a lot of sex - enough to be able to practice undoing a girl's shirt with one hand. She needed to be memorable, she needed to show him that despite dressing as a schoolgirl, she had the sex appeal of an adult.   
She used the grip of her legs around his waist to grind her hips up against his crotch, making him moan against her neck where his lips were currently attached. His lips began to navigate further down as more of her shirt came undone, and, not for the first time, Annie loved how small she felt in Jeff's arms. She felt protected, safe and adored.   
Soon, her shirt had completely fallen off her, kept on only around her arms, revealing more of her white lace push up bra that was struggling to hold her breasts in at this point.   
Memorable, she wanted to be memorable.   
"Sir," Annie breathed. "Mr Winger," She cleared her throat. Jeff looked up from where he'd been pressing wet kisses above her belly button, his eyes slightly darker with lust.   
"Yes Miss Edison?" He breathed out.   
"Would you sit in your chair for me? Want to ride you," She suggested. The costume was giving her confidence she didn't know she had. Annie very rarely requested what she wanted in the bedroom, it was something she was getting better at the more often she had sex (which wasn't that often), but having Jeff so obviously wanting her was sending her on an adrenaline kick that made her feel like she could do anything.   
Jeff let out a shaky breath at her request. "Well since you asked nicely," he breathed. He stood up and Annie released him from the hold of her legs. "You stay on my desk for now though," He added in instruction. He got down onto his knees and gently pulled Annie's underwear off from under her skirt. Annie's breath hitched as she watched him slide it down over her legs, choosing to keep the socks and shoes on. He then shucked the skirt up a little and before Annie could even be modest about him seeing her so bare for the first time, his mouth was attached to her hood, making her cry out. She tangled her fingers in his hair and threw her head back. Somehow she'd never pictured Jeff Winger as a woman-centred foreplay kind of guy, so this was a very pleasant surprise. And Christ was he good at it. If Annie didn't want to ride him so bad she'd let him stay down there all day.   
"You're so hot," Jeff breathed against her, slowly sliding in one finger, making Annie whimper. "Coming here to my office, God you knew just what you were doing to me Annie," he continued. "Got me wrapped around your finger, couldn't stop myself if I tried," he confessed and it was making Annie dizzy in combination with his now two fingers pumping in and out of her.   
"Jeff I-" she gasped out but then let out a guttural groan when his fingers abruptly stopped.   
"That's not my name," He purred, biting her thigh. Annie was pretty sure she could finish just from him talking to her like that.   
"Mr Winger," She corrected herself breathlessly, looking down at him. He smiled up at her and then continued his movements with his fingers, except now he curled them and paid incessant attention to her sweet spot.   
"Christ, sir, please, I'm gunna... I want to," she tried to get out and Jeff seemed to understand because he soon pulled them out. He stood up and kissed her, and Annie was relieved to notice she didn't taste that bad.   
Jeff walked around to the other side of his desk, stripping down to just his boxers. Annie watched him hungrily. He was all hard muscle, so much older than her, so much more manly than anyone she'd slept with. It was a lot to take in and Annie could hardly believe she was allowed to look, let alone touch.   
She swung herself around so she was facing his side of the desk now. She reached forward before he could sit, gently tugging his boxers down so they fell to his feet. Her eyes were looking up into his. She felt like she might make an embarrassing face if she looked straight at Jeff's dick, especially because he was still so much taller than her, even with her sitting on his desk, her face wasn't that far away from it. Instead she slowly dragged one hand down his sculpted body, letting her nails scratch a little at his lower stomach, making him gasp. Still looking up at him, she wrapped her hand around his dick, and began to pump slowly. He was very big in her hand, and now that she had a general idea of that, she felt confident enough to look down at it.   
Annie had never really thought of penises as attractive. When she was younger she'd wondered if that had made her a lesbian, but she'd realised she didn't find vaginas attractive either. Genitals weren't nice to look at.   
Well, except for Jeff's.   
It was clear he kept himself well trimmed. And he was big, and fully hard, and it represented all she'd wanted for so long that maybe it could have been the ugliest dick in the world and Annie would have thought it was hot.   
"You good?" Jeff asked through breathy moans. Crap, maybe her hesitation had shown. She was going for memorable.   
She briefly let go of him for a moment to reach around and unclasp her bra. She watched Jeff's eyes gaze over her, and for a second she wondered if she'd had the same overwhelmed expression when she'd looked at his dick. She reached around him and pushed against his bum to move him forward to her. She'd only ever seen this in porn, and she could do this really badly, but she was going for memorable here.   
She slowly maneuvered her breasts to wrap around Jeff's dick, enclosing it between them. She let some spit fall from her lips onto the head of it, and began to slide up and down.   
"Holy fucking shit Annie," Jeff gasped, shock and pure pleasure clear on his face. "You're...wow," he groaned. At least it was having the desired effect, Annie had never felt more confident and sexy.   
Jeff gently pushed her back to lean down and kiss her. It was a heated kiss, their tongues sliding together before Jeff moved down to suck her nipple into his mouth. Annie moaned.   
"Mr Winger please," She begged once more. Jeff moved his mouth away and sat down in his office chair. Annie reached behind her to begin undoing her skirt, when Jeff quickly reached forward and grabbed her wrists.   
"Leave it on Miss Edison," he commanded. Annie swallowed thickly and nodded in assent. She hopped off the desk and looked down at Jeff, who was holding his dick at the ready. She could see in his eyes, as he looked her up and down whilst he rolled on a condom from his desk drawer, that maybe he was starting to worry they'd gone too far. Annie couldn't have that. She put her hands on Jeff's shoulders, and straddled him, slowly sinking down to completely sit on him. They both moaned, their foreheads resting together and their lips brushing.   
"God you feel so good," Jeff panted softly, his hands holding her hips steady.   
"You're huge," Annie breathed back and Jeff chuckled wryly.   
"Porn teach you to say that?"   
"I mean it, never had anyone this big inside me," Annie reassured.   
"Christ Annie, I'm inside you," Jeff gritted out, moving to bite down on her shoulder once Annie's ass was firmly rested against his thighs. Annie was now really getting dizzy with it. She felt so full. Full of the man she cared so much for, the man who she felt the safest and adored around, even on days when he didn't really show it.   
Annie began to rotate her hips, trying to find an angle that felt amazing for both of them. They both let out a deep moan at a certain spot so Annie began to focus her rotations there before she began to bounce. With every smack of her bum against Jeff's thighs she let out little "yeah's," and he either swore or said her name. It was all a rather loud affair and Annie was relieved Hickey was in class right now, and she was relieved Greendale was not the kind of school where the students would come to their teacher's offices to ask anything.   
Annie felt a part of herself almost want someone to walk in, but she tucked that exhibitionism away to be analysed another time.   
Her arms were wrapped loosely around his neck and she was sure she'd have bruises on her hips from how tight Jeff was holding her. She didn't mind. She wanted something to look at later to remind herself this wasn't a dream. With that thought, Annie moved to suck a mark to Jeff's left pec, bending slightly to do it but keeping her rhythm up. Jeff hissed but moaned still, so Annie assumed he liked it.  
He moved to wrap his right arm around her to bring her close, they were chest to chest now. Annie moaned and rested one hand on his large bicep. "God I love your arms, so strong," She whimpered. "Love your hands-" She cut off her sentence with a gasp as Jeff now used his free hand to slide between them and rub his thumb over her clit. "Definitely love your fingers," She giggled breathlessly.   
Jeff smiled against her lips, capturing them in a kiss again. "Annie I'm gunna-" He panted.   
"Me too," She promised and only seconds after she'd finished saying it, her orgasm hit her hard, making her clench around Jeff. She felt his body tense against her and he held her hips down to stop her movement, his eyelashes fluttering shut as he rode out his own orgasm.   
The two sat there for a few moments, just panting. Jeff tilted his head slightly so their lips connected. It wasn't much of a kiss, it was simply just having their mouths pressed together, they were both too exhausted to put too much effort into it. But it was still really nice, it felt tender and soft.   
"That was the hottest thing I think I've ever done," Jeff whispered and Annie couldn't help but beam at him. "Don't look so smug," Jeff chuckled softly.   
"I just had sex with sex crazy Jeff Winger and I was the best, I'm allowed to be smug," Annie smiled softly. She squeezed his shoulders and slowly stood, releasing him from inside her, it had been starting to get uncomfortable.   
"I am not sex crazy," Jeff protested, his eyes following her as she began to get dressed.   
"You have a lot of sex," Annie shrugged. "At least now I know this will be memorable for you."   
There was a pause. "Is that why you did this? To sleep with me and be known as the best?" He asked.   
Annie's face turned pink. "You know me, love a gold star," She murmured, focusing on buttoning up her shirt. Jeff was suddenly standing and he grabbed her hands.   
"Annie you didn't have to do all this for me to think you're the best," He murmured. Annie looked up at him. His expression looked like pity, or confusion. In fact maybe his expression was just unreadable, but Annie didn't like it.   
"I did all this so you'd see me as a sexy woman who could do this sort of stuff, so you'd take me seriously and see I'm not a pure little kid," Annie explained, not moving her gaze from him. Jeff seemed to consider this for a moment.   
"Annie I've always thought you're sexy, it's been a problem for me basically since I met you," He pointed out and Annie felt her face going pink again. "And sure, yeah you proved to me that you're confident and definitely not pure in the bedroom," He chuckled softly, and dammit Annie was sure she probably looked like a tomato, which wasn't the confident look she was going for. "But next time, only do stuff if you want to do it, not to prove anything," he finished.   
"Next time?" Annie asked hopefully.   
"Well yeah, we've given into this now, no point stopping if that's how amazing it is," Jeff chuckled, looking away from her to get dressed himself, and Annie could tell he was a little nervous. Jeff may be the confident one between them when it came to sex, but emotions were Annie's forte.   
"Okay, next time I want to be wined and dined then," Annie smirked, turning him around and beginning to button his shirt up for him. "I just gave you memorable sex, you give me a memorable date," She challenged.   
Jeff licked his lips, and for one heart stopping moment Annie thought he was going to say no.   
"Of course Miss Edison," He smiled, the fond smile Annie had noticed he didn't give many other people. Any other people if she was really hopeful about it.   
Annie finished his buttons then leaned up and kissed him deeply. He wrapped his arms around her and held her close.   
"God I'm glad I didn't stop you," Jeff whispered against her lips.   
"Me too," Annie smiled. "In another timeline you probably did," She chuckled.   
"You've been spending way too much time with Abed."


End file.
